Search Cottages in Chappaquiddick Island

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 101 Cottages in Chappaquiddick Island with updated reviews, rates, and availability.

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (145)
"We spent about a month in this absolutely wonderful home on Nantucket. When we arrived, it was clear the house has been professionally cleaned and was spotless. The kitchen is great for cooking for meals in. The tv room has a ton of natural light & was a great place to hang out as a family. There are 2 bedrooms, one on main floor which is easily accessible and 1 in the loft which is a steep staircase (fine for us as we have no mobility issues but bear this in mind). The little patio on the side...
Renovated Cottage off Main Street- Great Location

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (111)
"To stay a block from the beach and look out the window at the water is the ultimate vacation! Even in winter this place is warm and inviting! The hosts are caring and communicative - just the best! This cottage lets you do just that"
Steps to the beach with an ocean view,

Craigsville beach cottage located .4 walking distance to the Beach!

9.8 out of 10, Exceptional, (6)
"Courtney's house is in a fantastic location. Easy access to downtown Hyannis for shopping and nightlife, walkable to beaches with fantastic swimming. The house is newly renovated, but maintains the charm of a home with some history in the area. Sweet backyard with a patio set up to enjoy outdoor dining and lounging. The neighborhood feels secluded, but is really near all the summer happenings. Well stocked kitchen, smart use of a small space. I can't say enough about our fantastic stay. I have...
Craigsville beach cottage located .4 walking distance to the Beach!

Gorgeous Cottage steps from the beach

9.0 out of 10, Wonderful, (12)
"Perfect getaway"
Gorgeous Cottage steps from the beach

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (64)
"Great property in great location on Cape Cod. 30 min drive for ferry to Nantucket. 2 minute walk to Beach within neighborhood. Cozy and quiet. Would not hesitate to stay again. "
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

10.0 out of 10, Exceptional, (20)
"Maushop is the perfect place for a family getaway right on the ocean. The property was clean and spacious for a tiny cottage. We had a wonderful time."
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

6.2 out of 10, (17)
"We did not stay. Place was a dump No one has called us We are not paying It is illegal not to have carbon / smoke detectors We went to condos at new seabury"
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

10.0 out of 10, Exceptional, (23)
"This is our second time at this property. It is as described. Beautifully updated. Location could not be better!! One street away from where my grandparents used to live. Such great memories!"
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

Exquisite Oceanfont Cottage at Madaket Beach!

10.0 out of 10, Exceptional, (12)
"Fantastic property well aportioned and great communication. Would highly recommend"
Exquisite Oceanfont Cottage at Madaket Beach!

2-bdrm Cottage | Close to Everything | Pet Friendly

9.8 out of 10, Exceptional, (9)
"Beautiful cottage, very clean and comfortable. Very peaceful and quiet! Weather wasn't the best for sitting outside to enjoy nature, but it was beautiful nonetheless. Bonnie is an excellent host! We definitely will return!"
2-bdrm Cottage | Close to Everything | Pet Friendly

★The Islander | Steps From Water, Fire Pit, AC★

10.0 out of 10, Exceptional, (44)
"I was travelling with my 3 sisters from Canada heading towards Martha's Vineyard for a sister's reunion. We all appreciated the cleanliness and the attention to detail. The space was well appointed. The fridge ice maker did not work well so having some ice cube trays would have been helpful. I highly recommend The Islander."
★The Islander | Steps From Water, Fire Pit, AC★

Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach

9.8 out of 10, Exceptional, (102)
"Comfortable cottage. Great location. "
Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

8.8 out of 10, Excellent, (26)
"The property was great and walkable to the beach, but needs a few upgrades. "
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

10.0 out of 10, Exceptional, (25)
"we stayed on Chappy for a family wedding. The cottage was great. No issues, very comfortable and close proximity to the festivities! Thanks!"
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

12 VINEYARD VIEW - FULLY RENOVATED

9.6 out of 10, Exceptional, (40)
"We had such an amazing time staying here! The location is perfect and has amazing ocean views right from the house. Everything was super clean and well maintained. We will definitely be coming back! "
12 VINEYARD VIEW - FULLY RENOVATED

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (201)
"Loved the rental. Perfect setting, loved being able to walk 2 minutes and be on the beach! So much nicer than a hotel room, very clean and comfortable for the four of us. Steve was a very kind and helpful host!"
Steps to the Ocean! Perfect Location!!!

2 Bedrooms + Loft - Sleeps 6 in Beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (96)
"Clean, cozy, well-located, it's a great spot for folks who want to stay together and have separate space at the same time. The adjoining unit makes this possible and unique in that way. "
2 Bedrooms + Loft - Sleeps 6 in Beds but max 4 adults- 5 Blocks to Town

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (19)
"As advertised. Photos are accurate, as is description. Short walk to town/supermarket, cafes and more. Accommodations are clean, well-kept, and basically brand new. Thanks! Brett Star"
Cozy New TimberFrame Vineyard Haven!

One Bedroom Private Cottage on Large Quiet Property.

9.6 out of 10, Exceptional, (4)
"I kind of don't want to leave a good review because it will likely result in this property becoming too hard to book. jk. Seriously, everything about my experience was beyond excellent from the booking process to meeting the owners. The pictures honestly do not do it justice. It is a beautiful cottage that is far enough away from the main house to give you all the privacy one may need/want. It is in walking distance to the Vineyard Haven ferry dock and the retail in that area. The owners were...
One Bedroom Private Cottage on Large Quiet Property.

Charming Post and Beam Cottage! Walk to the beach, Tennis, Bike Path, & Shuttle

9.8 out of 10, Exceptional, (28)
"We loved our stay. The cottage was very well equipped, clean and private (even though it is a guest cottage on the back of the property). The owners were so nice and willing to help with dinner recommendations and island suggestions. We’ve been coming to Nantucket for 25 years and would highly recommend this property! We loved our family vacation in this beautiful location close to walking trails, 40th Pole, Madaket beach (Millies) and public transportation to town."
Charming Post and Beam Cottage! Walk to the beach, Tennis, Bike Path, & Shuttle
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chappaquiddick Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chappaquiddick Island

Chappy Summer Cabin!

8.2 out of 10, Very Good, (33)
"Great host , amazing property "
Chappy Summer Cabin!

Sleeps 12, amazing view, tennis court, basketball court, beaches

9.6 out of 10, Exceptional, (37)
"It was a great place to hangout with family members. I lot of places to plop down with a book, a lot of things to do to keep people busy - just a great time."
Sleeps 12, amazing view, tennis court, basketball court, beaches

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (162)
"Girl at front desk was awesome!!!"
The price is SAR 441
SAR 504 total
includes taxes & fees
30 Mar - 31 Mar
InnSeason Resorts Captain's Quarters
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your cottage in Chappaquiddick Island with Expedia?
Reserving a cottage in Chappaquiddick Island is as simple as deciding on your travel dates and picking an ideal place for a getaway in the outdoors. From ritzy retreats to inexpensive stays and cottages that offer amenities like laundry facilities, Expedia has something for all tastes. As for epic deals? We’ve got your back!
How can I find cheap cottages in Chappaquiddick Island?
Expedia can help you locate cheap cottages in Chappaquiddick Island. To book your perfect stay in just a few clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.